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The phrase "pessimistic with" is correct and usable in written English
You can use it when you are describing a person's attitude or outlook on a specific situation. For example, "My friend's attitude towards the situation was very pessimistic with no hope of a good outcome."
Exact(28)
Older people tend to be even more pessimistic, with 62 per cent predicting a crash in the next 12 months.
The OBR's view of the economy is significantly more pessimistic, with the 'cyclical' impact of the downturn lasting much longer.
Most Americans are not pessimistic, with substantial majorities saying they expect economic conditions to remain about the same.
Older people are the most pessimistic, with 53% of those aged over 55 believing their circumstances will deteriorate, against 9% who expect things to get better.
Those numbers are quite pessimistic, with most economists predicting economic growth of only about 2 percent over the next couple of quarters.
New Challenge for Lucchino Seven men sat in a Boston hotel room as day turned into evening last Thursday, growing increasingly pessimistic with each passing hour.
Similar(32)
After analyzing the results the researchers identified three patterns of personality: I-pessimistic with perceived low self-efficacy (N=90), II-optimistic (N=40) and III-mixed with perceived low self-efficacy but low vulnerability (N=60).
He will contrast the Conservatives' "pessimistic isolationism" with Labour's "genuine and hard-headed multilateralism".
The authors of the study consider an "optimistic scenario" with small increases in trade costs between the UK and the EU, and a "pessimistic scenario" with larger increases.
In it he examined society from the standpoint of a savage and gave the clearest statement of his pessimistic philosophy with its emphasis on willpower and struggle.
Pobedonostsev was a dry, reserved, and deeply pessimistic ascetic with almost no close friends, except for the novelist Fyodor Dostoyevsky, who died in 1881.
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Since I tried Ludwig back in 2017, I have been constantly using it in both editing and translation. Ever since, I suggest it to my translators at ProSciEditing.

Justyna Jupowicz-Kozak
CEO of Professional Science Editing for Scientists @ prosciediting.com